Reacción #42566

Ecuación de reacción

methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate

thiazole

n-butyl lithium

→

methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

Rendimiento 99.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaThe mixture was then heated at 80° C. for 2 h, at which time it
3. 3
   Temperaturato cool
4. 4
   Otropartitioned between ethyl acetate and water
5. 5
   LavadoThe organic layers were washed with brine
6. 6
   Secadodried (magnesium sulfate)
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was chromatographed on silica gel

Procedimiento

To a −78° C. solution of thiazole (1.2 g) in THF (25 mL) was added n-butyl lithium (1.6 M in hexanes, 10 mL). The mixture was stirred for 30 min and then allowed to warm to 0° C. in an ice/water bath. Zinc chloride (1M in ethyl ether, 40 mL) was added and the mixture was stirred for 1 h, at which time methyl 3-[(dipropylamino)carbonyl]-5-iodobenzoate (5.1 g) in THF (20 mL) was added, followed by Pd(PPh3)4 (palladium tetrakis triphenylphosphine) (0.68 g). The mixture was then heated at 80° C. for 2 h, at which time it was allowed to cool and partitioned between ethyl acetate and water. The organic layers were washed with brine, dried (magnesium sulfate), and concentrated. The residue was chromatographed on silica gel using ethyl acetate/heptane (50/50) to give 4.5 g of methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate.

Fuente